In 2001, Bledsoe was the starting quarterback of the New England Patriots when he suffered internal injuries after taking a big hit by Jets linebacker Mo Lewis in Week 2. Little did anyone know that Lewis’ tackle would change the course of Patriots history, immediately ushering in the Tom Brady era.

Brady, a sixth-round pick of out Michigan, went 11-3 in place of Bledsoe in 2001 and has gone on to author a Hall of Fame career.

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Romo might be staring at the same situation after the veteran quarterback suffered a back injury in the preseason and has since lost his starting job to Dak Prescott, a fourth-round pick who has guided the Cowboys to their longest winning streak in franchise history.

Bledsoe joined Colin Cowherd on “The Herd” on Monday and discussed what must be going through Romo’s mind.

“It’s the absolute definition of bittersweet,” Bledsoe said in the video above, “because as a teammate you’re really happy for your team. And that’s genuine. I was genuinely happy for my teammates in New England when we were winning and went on to win the Super Bowl that year.”

But as happy as Bledsoe was watching the Patriots head toward the sport’s biggest stage, he said it was still difficult not contributing on the field.

“But at the same time it breaks your heart,” Bledsoe said. “You put all this blood, sweat and tears into a career, and you kind of have been the guy for a long time, and it breaks your heart to know your team is going out and having success without you.

“It’s kind of a helpless feeling being on the sidelines. You want to contribute, but you’re used to being the guy in the middle of the action and now you’re not.”

Though Romo is currently holding the clipboard, Cowboys owner Jerry Jones has made it clear he expects the 36-year-old to be ready at a moment’s notice. For now, Romo is saying all the right things and is accelerating Prescott's learning curve on the sidelines.

Will Romo's bittersweet situation end the same way as Bledsoe's? With the Cowboys hoisting the Lombardi Trophy?